1. Field of the Invention
The present invention relates to novel 3-iodopropargyl ester of carbamic acid, and to use of the ester as a microbicide and preservative.
2. Description of Related Art
A large number of commercial, industrial, agricultural, and wood products are subject to microbiological attack which reduces or destroys their economic value. Examples of materials that may be subject to degradation are surface coatings, wood, agricultural seed, leather and plastics, including flexible plastics.
Examples of aqueous systems containing organic materials subject to attack are latexes, surfactants, dispersants, stabilizers, thickeners, adhesives, starches, waxes, proteins, emulsifying agents, detergents, cellulose products, and resins formulated in aqueous solutions, emulsions or suspensions. Such products frequently contain relatively large amounts of water.
The temperature at which these products are stored and their intrinsic characteristics make these products susceptible to the growth of microorganisms. These microorganisms can be introduced during the manufacturing of these products by exposure to air, tanks, pipes, equipment, and humans and/or during their use from multiple openings and reclosures of packaged products and by the introduction of contaminated objects to stir or remove material.
Microbiological degradation of aqueous systems containing organic materials may manifest itself in a variety of problems, such as loss of viscosity, gas formation, objectionable odors, decreased pH, emulsion breaking, color change, and gelling.
Another objectionable phenomenon occurring in industrial process systems involving water is slime formation. Slime consists of matted deposits of microorganisms, fibers and debris. It may be stringy, pasty, rubbery, tapioca-like, or hard, and it may have a characteristic odor that is different from that of the liquid suspensions in which it is formed. The microorganisms involved in its formation are primarily different species of spore-forming and nonspore-forming bacteria, particularly capsulated forms of bacteria which secrete gelatinous substances that envelop or encase the cells. Slime microorganisms also include filamentous bacteria, filamentous fungi of the mold type, yeasts, and yeast-like organisms. Slime reduces yields in paper production and causes plugging and other problems in water systems.
Compounds containing an iodopropargyl group have shown fungicidal and bactericidal activity. U.S. Pat. No. 4,259,350 teaches the use of iodopropargyl esters of carboxylic acids and sulfonic acids as microbicides. U.S. Pat. No. 4,592,773 claims substituted propargyloxy-acetonitrile derivatives as agricultural fungicides. U.S. Pat. No. 3,660,499 discloses aryl-3-iodopropargyl formals as fungicides. U.S. Pat. No. 4,639,460 discusses the fungicidal properties of N-(1-iodopropargyl)-thiazolidinones. U.S. Pat. No. 4,616,004 enumerates the uses of 1-iodopropargyl-3, 4-disubstituted-.DELTA..sup.2 -1,2,4-triazolidin-5-ones as agricultural fungicides. U.S. Pat. No. 3,923,870 teaches the use of urethanes of 1-halogen substituted alkynes as fungicides, particularly when used in surface coating compositions such as paint formulations. These urethanes are prepared using organic isocyanates. Organic isocyanates have the unique disadvantage of being manufactured from phosgene, a dangerous and difficult chemical to handle. Once prepared, these organic isocyanates are difficult to store and handle because of their sensitivity to air and their propensity to react with water to produce hydrochloric acid fumes. Some of these isocyanates can also produce chronic health hazards. The present invention, as will be shown, uses inorganic cyanates which are relatively safe to handle.
Furthermore, the urethanes divulged in U.S. Pat. No. 3,923,870 differ from the compounds of present invention, in that, the former have an alkyl group of a 1-20 carbon chain attached to the nitrogen atom and the latter do not. In addition, these urethane compounds do not possess effective bactericidal utility.
It is an object of the present invention to provide a 3-iodopropargyl ester of carbamic acid having effective batericidal utility.
It is another object to provide a method for inhibiting the growth of microorganisms in aqueous systems.
It is still another object to provide a method for inhibiting the formation of slime in an aqueous liquid.
It is a further object of the present invention to provide a method for inhibiting the growth of microorganisms on a substance susceptible to deterioration or disfiguration by microorganisms.
Additional objects and advantages of the invention will be set forth in the description which follows, and in part will be apparent from the description, or may be learned by pratice of the invention. The objects and advantages of the invention may be realized and obtained by means of the combinations particularly pointed out in the appended claims.